Steroids and related products. XXXIX. The functionalization of the 17-methyl group of 17α-methyl steroids. II. The synthesis of 12α,171-epoxy-17α-Methylprogesterone (cas 1046-28-2) and of 20-oxygenated 17α-hydroxymethyl steroids

Add time:07/23/2019    Source:sciencedirect.com

The functionalization of the 17-methyl group of 17α-methylated 20-oxygenated steroids is reported. Two methods were employed for that purpose: the Jeger reaction with lead tetraacetate, applied to a 12α-hydroxy 17α-methyletianic ester, leading to a 12,171-epoxide and the photolytic Barton reaction, applied to the corresponding 12-nitrite, and leading to a 171-nitroso derivative which was transformed into a 17β-methoxycarbonyl lactone of a 12α-hydroxy 17α-etianic acid. The 17β-ester group of this compound can be selectively hydrolyzed and the lactone group can be reduced to a 12α-hydroxy 17α-hydroxymethyl steroid. The synthesis of 12,171-epoxy-17α-methylprogesterone is also described.

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